When Your Dreaming with a Broken Heart
by DoodleRave
Summary: The year is 1957, and the life of Wade Cry-Baby Walker has been nothing but hardship after hardship. The world is changing around him and through a sudden mishap, He finds himself at the company of some strange people with even stranger ways. What is this new generation of people? Cry-BabyXOC
1. Chapter 1

"DAMNIT!" Crybaby slammed the hood of his car down loudly. Frustrated as the steam flowed from beneath its hinges.

Him and his two gang members ; Milton and Hatchet-Face; stood around the car, their cheerful high of the school day being over now sizzling to a deep depression.

"What's wrong with it man?" The only other male in the Crybaby gang, timidly scratched the back of his greased hair. He would have offered to help Crybaby, but he was always a bit touchy about people getting to familiar with his rides. He never did get over that incident where Baldwin set fire to his motorcycle.

So Milton thought it best to stand back. Crybaby didn't even look up from the car. He just bared his teeth, neck bulging, eyebrows furrowed, eyes glaring deathly, and growled out his response. "HELL IF I KNOW! Damn thing's been acting funny all week! First the belt broke off, then the back tire blew out, NOW THIS!"

He kicked his boot into the front bumper, leaving a small dent. He used to worship this car. Now it just reminded him of his downward spiral in life. First his bike was set ablaze, then sent to jail, Wanda left the group to move to the big city, Pepper got Married and moved out with her kids and quit school to take care of the new baby, then Allison...oh Allison. To this day his heart burns alive thinking of her, but she was gone. He didn't like to recall the memories. In fact he did his best to block them out at all cost. Now his last ride sat in front of the school building, smoking and sputtering its way to death.

"Well...uh...sorry Man. Is there anything we can do?" Milton tried to ease the tension.

"Yeah, wanna just take the bus?" Hatchet-Face laced her fingers with Milton's and slowly started to pull him towards the approaching School Bus drove by Wanda's dad.

Cry-Baby lifted the hood once more and tried to wave the smoke away to look into the car again with dead eyes.

"Nah. You guy's go ahead."

"You sure?" Milton asked. Hatchet-Face tried to shh him. Obviously Cry-Baby wasn't going to just leave the car here no matter how much he hated it, and he seemed to be wanting to be left alone now.

"Yeah...seeya." He muttered emotionless.

They looked at each other with worried eyes but turned when the Yellow Bus squeaked to a stop behind them, the door opening to the same smiling man who greeted them kindly as they climbed inside and drove away.

While Cry-Baby tinkered with the mechanisms, the rest of the student body walked out from the front doors of the building. Smiling, laughing, saying goodbye. He grit his teeth at the sounds. All of them being so happy. It made him sick. It was days like this, he wondered why he came to school at all. His freshman year seemed so long ago, three years in fact. Now he was a senior. Somehow he had barely skimmed by in class to pass. Thanks to she-who-will-not-be-named. It was her idea anyway. She wanted him to do better for himself. He never understood that meaning, but he stayed, he studied, hell he even tried not to sleep, just because she asked him to. He loved her that much, but...it Wasn't enough.

Crybaby pushed the lock of greased black hair that had fallen in front of his face back, and stood up to arch and pop his back, which was now sore from leaning over the car for so long. He pulled a toothpick from his pocket and jammed it between his teeth. A small habit he developed after doing it on purpose a few times attempting to look cool, now he usually needed one everywhere he went.

He pulled off his leather jacket and placed it on top of the car, his white t-shirt had the sleeves torn off showing his cry-baby and native American tattoos.

What was he going to do now...

As if fate itself heard his desperate thoughts, a small tap on his back and someone clearing their throat made him turn around. His eyes glazed over to their normal cold demeanor to stare at the sudden approached. What square dared to touch him.

She was barley 5'6. Her over-sized white button down shirt ruffled and crinkled as it tucked into her pale cream, knee length skirt. Her hair, which was a warm brown and extremely curly, was braided on each side behind her ears reaching just below her shoulders, and small black glasses sat atop her nose framing bright blue curious eyes.

What kind of square was this? She looked no older than 15.

"what.." He growled.

She averted her eyes to the car nervously. "Um...Are You having trouble?"

He bit down on his tooth pick. "Im having a picnic. What's it look like!"

She winced at his tone and bit down on her pink painted lip.

"What do you want kid I don't got all day."

She gulped and looked back up to him. "I know someone who can help."

"huh?" Now he was confused.

She pointed to his car. "I know a mechanic who has a tow. He can fix it for you."

"And tell me Sugar. Why would a little kid square like you want to help me huh?"

He stood over he with his arms crossed. If he was honest, he would say he did need the help, but he was having a shit day so he felt like being a jerk.

The girl averted he eyes and twirled a bit of her curly hair in he fingers nervously. He was actually feeling a bit guilty for making her this scared.

"Well...i..umm...you Looked like you were really sad about it."

"So you just thought you'd come over and help Ol' Cry-Baby huh? Aren't you scared? Don't you know anything about me or what I've done? Little girls like you should stay away from guys like me OK?"

She bit down on her lip again, she took in a deep breath before forcing herself to look up at him again with more determined eyes. " Mr.. Cry-Baby, Im not a little girl...and...and My daddy said never judge someone until you meet them yourself. So...So I don't care what people say about you." She gulped and held out her hand with a flush on her cheeks. "My name's Lilly-Anne Ferguson. It's nice to meet you."

His eyes stared wide down at her outstretched hand, his eyebrow arched in complete bafflement. This is no ordinary square. Hell she's not a Drape or a Square. So what is she?

She stared at him hopefully, arm staring to shake a little from being held out so long.

Finally he looked back at her face before twirling this toothpick with his tongue and gently shaking her hand.

"Your weird kid." She smiled big and walked over to his car scanning it with her eyes.

"So who's this guy you know..How much does he cost?" His tone seeming much better and less aggressive. The girl had broken his tough act with her oddness.

"Oh he's pretty cheap, but I don't know how long it will take him to fix it. Are you OK to walk a little ways?"

She looked up at him through her lenses and smiled already knowing his answer.

"Walk...how Far?"

Hello everyone. Thanks for reading my first Fanfiction. Truthfully i wouldn't have made this Fanfiction is there had been more Cry-Baby submission, but the options here were very few so i figured why not. ANYWAY!

I would like to hear your thoughts about this and please be truthful im a big girl, no need for sugar coating. Let me know in the reviews if you'd like me to continue, or if there is anything i can improve on?

Thank you.

-Doodle


	2. Chapter 2

Ok so I'm going to give chapter 2 a shot. So here we go. Sorry if its crap and that it took so long to continue.

The sun started to set through the rows of oak trees, turning the bright blue skies into oceans of orange and pink. Days like this made Crybaby wish he was on his dearly missed bike. Unfortunately his daydream was cut short by the harsh reality of his location. Where was he? Walking. WALKING. Walking in the damn woods! With a skipping, whistling kid, that kept trying to have conversations with him for what seemed like hours.

He rolled the toothpick in his teeth, occasionally biting down to scowl at the girl. What was her name again? Amy?..Mary?

"It's just up ahead. Up on that hill." She pointed upwards further in the woods. All Crybaby could see was trees, trees, and more trees. He was starting to think this kid was secretly a monster dragging him out in the middle of nowhere to eat him alive. He almost chuckled at that thought but did not give her the satisfaction. He just grunted and glared at the back of her head.

"I don't see anything. You better not be messing with me kid."

She turned to look up at him again and readjusted her glasses. "I'm not i promise. Don't worry."

She flashed a smile and started skipping up the hill again. He let out another grunt and followed her, within distance in case his silly cannibal thought might be true.

Sure enough Crybaby actually started to see the top of a house once the trees started to space out more. Well, house is not the right word, It was tall and oddly shaped. It sort of reminded Cry-Baby of an old abandoned church, but it had, what looked like, a tower made out of grey and white bricks built onto the left of it. Perhaps it was even a clean shade of white, but green moss and vines had dinged the building into a dirty green and brown color. Most of the windows were cracked and seemed to be put back together with tape. Its roof had chunks of missing shingles and a few boards nailed to it. On the front porch there was a rocking chair, a porch swing, and at least a dozen wind chimes made out of rusty spoons and empty painted glass bottles.

What the hell kind of place is this? She actually lives here? He thought to himself. His toothpick long dropped from his mouth in shock. He was right...she was a monster going to eat him. Who else but monsters could live like this?

The girl..damn what was her name again? Put her hands on her hips and smiled. "Home sweet home. It's not much, but its comfy. Now where is..."

Her question was cut short by the sound of music playing so loud it caused Cry-Babys heart to jump clear up into his throat. All the birds in the area to flew away in panic, and even the girl held a hand to her chest in fright.

The music blared and after a moment Cry-Baby could actually distinguish the tune. The song was Elvis Presley's new hit Heartbreak Hotel.

"Oh no no no no NO!"

The girl seemed to glow bright red with rage and stomped off into the direction to what looked like an old barn off to the side of the house. Her braids flying behind her as she picked up speed, obviously forgetting Cry-Baby's presence entirely.

Out of curiosity he followed her to the barn. Maybe another monster like her waited inside. At least it had good taste in music. She pushed with all her might to get the front door open, digging her shoes into the dirt. The music blared loudly from inside and even the leaves on the vines that engulfed the barn shook with every beat. After finally getting the door open enough for her and him to squeeze inside, Cry-baby almost felt the need to cover his ears from the volume, but his eyes wandered the inside in wonder. The dirt floors were covered in old patterned rugs that over lapped, barley leaving any cracks for the dirt to show through. Along the walls and hanging from wooden beams were dyed bed sheets in multi- colors.

Cry-baby could see an old record player spinning off in the corner. A large microphone was bent into the old brass horn to pick up the sound that bellowed from the small Amplifier next to it.

The little monster girl looked around frustrated in search of something. Perhaps Cry-Baby was getting old but for once in his life he understood the meaning off "Too Loud". Wow did he really just think that?

Suddenly a green wine bottle fell from the sky and crashed onto the rugs and dirt along the floor, scattering bits of glass.

After suffering ANOTHER heart attack from the crash, did the girl and Cry-Baby look up from wince the bottle fell. Up high, tied to the wooden beams was a hammock and what appeared to be a person swinging in it.

"Are you crazy get down from there!" The girl screamed with all her might trying to make herself be heard over the loud music and after a long minute, someone in the hammock reached up an arm and wrapped a hand around one of the ropes hanging from the beams and gave it a tug. A noise rumbled from the beams and the hammock slowly started to lower. How the hell was THAT happening? Cry-Baby stared up into the beams looking for this contraption that was lowering the hammock down but it was too dark to see anything. Maybe they were witches, not monsters.

After it was about 5 feet from the ground the invisible roof contraption made a loud squeak and crack, and some smoke puffed from the darkness. Within seconds the hammock dropped with speed plopping onto the rug covered dirt. The body within the hammock let out a groan and a few swears.

The little girl ran over and tried to free the body from its trap within the tangled cloth.

"Jeez. Have you been drinking?"

A giggle erupted from the mass and it sat up, dropping the sheet to the ground revealing another girl. One much older and...drunker.

She smiled wide at the kid and pulled her into a hug. "Lilly! How was school!" She screamed over the still blaring Elvis.

Lilly grunted and tried to pry out of the drunk girls arms. She glared at her and squished her face between her hands. "Why on earth are you smashed in the middle of the day? Where is Phil?"

The drunk girl shrugged and stood wobbly to her feet stretching. Crybaby's mouth gaped open slightly. His eyes trailing down her. Her skin was slightly tanned from the summer sun, her face was rounded and almost boyish with freckles dotting across her cheeks and nose. Her hair was a much more copper shade that Lilly's and was cut right down to the nape of he neck. It was without a doubt the shortest hair Crybaby had ever seen on a girl. In fact he had never in his days seen a girl with such a mess of hair and clothes. He thought girls were into looking good, dressing nice, and wearing makeup. Even the drape girls didn't go outside without red lipstick on. No this girl might as well have been raised in a cave.

Her red plaid shirt was dirty and far to big for her, i might as well been a mans. A pair of grease and dirt smeared jeans that she had cut off at her knees were even more gender confusing. Was his really a girl?

What kind of circus had he gotten himself into. Looking at them both, he could see the slight resemblance in the face and hair colors, but nothing could make them look opposite that the square clothes on the little girl..and the ragged frocks on the other.

The drunken boy-girl-thing looked lazily over to the record player and started to dance while also trying not to fall over. The kid furrowed her eyebrows and pushed up her glasses once more before running over to the record player and quickly removing the needle, causing the music to stop with a squeak. The drunk female stopped moving and looked around confused. "Whad' happened to Tha King?" Thats when her eyes landed on Cry-Baby. An almost twisted shade of lime green looking him up and down, her face an intoxicated shade of red as she started to grin.

"Who's tha gangster?" She slurred. The kid stood between them and tried to keep the drunk from falling. "This.." She gestured to him with her eyes nervously, "Is Crybaby Walker. He goes to my school. That's why i need to know where Phil is."

The drunk girl furrowed her eyebrows and ran a hand through her mess of unbrushed hair. "Ummmmmmm...Phil?...He's...um.." She looked around the barn quickly and stumbled a little before looking back at the kid. " he was here a second ago...I dunno where he went." She shrugged and plopped onto the rug beneath her sitting crossed legged once again looking Cry-Baby over.

"No no no, you get up and go wash up i can't have you stumbling around all day." She pulled the now irritated drunk girl to her feet and made her lean onto her for stability. "You have to get sober!"

The drunk girl grumbled whilst the kid limped her out of the barn with Cry-Baby not far behind. She managed to get her to the porch before pushing her into the rocking chair. "Stay here ill get you some water." The kid turned to look back at Cry-Baby who waited in the yard, keeping his distance from the two. The girls blue eyes looked at him with guilt and a silent apology. "Sorry this will only be a minute. Phil should be around here somewhere and he will go pick up your car."

Before he could even open his mouth the kid had ran inside. He was starting to not like this idea more and more. From what he could tell this place was weird and he wasn't sure he wanted this Phil touching his car. He might be just as crazy if not worse.

"Is that ya real name?" The drunk girl called to him.

Startled he looked up to the porch to see her smiling lazily and still flushed from her booze intake. "Seriously is that your name?"

He glared at her. "It's what i go by."

She took no hint to his aggravation, or she just didn't care. She raised a curious eyebrow and leaned forward resting her chin in her hands. "So whats your real name?"

"None of your business."

Her smile stretched tauntingly and started giggling. Cry-Baby could feel his eyebrow start to twitch in anger. When she finally stopped she stretched her arms above her head and sighed before returning her gaze to him. "That's cute." She smirked

That's it, she has to die.

Before Cry-Baby could muster up the rage to smack her in the head with his boot, the kid came busting from the door, a glass of water in one hand, and some bread in the other. She forced both into the drunk-annoying-boy-girl's hands. "The bread will soak up some of that booze in you hopefully. Hurry up."

The drunk happily took a bite from the bread and swallowed some water. "I think Phil's in the back."

The kid rolled her eyes, "You could have said so earlier." and hopped down from the porch. She grabbed ahold of Cry-Baby's leather jacket sleve and pulled him with her to walk behind the house.

Back behind the house was a garage and a litter of car parts stacked in piles among it. A black tow truck sat in front of the shop and a pair of dirty booted feet hung from the window.

The girl released Cry-Baby and climbed up the steps of the truck to peek inside, pushing on the boots. "Hey! Phil don't tell me your drunk too! wake up you have work to do!"

Phil, Cry-Baby assumed, let out a grumbled before both boots retracted back into the truck and the door opened with a squeak. A tall lanky man in dirty grease smeared overalls stretched and popped his back. "Not drunk Lilly-Anne. Just havin a nap." He turned and looked at Cry-Baby with amusement. The man's hair was the same copper shade as the drunk she-he, but his eyes were the bright blue shade as the kid's. His copper hair seemed to have merged with his long, graying copper beard that concealed most of the bottom of his face, but his smile was quite easily noticed.

"Well evenin. What can i do for ya sonnie boy?"

Cry-Baby snapped out of his train of thought and was about to mention his car when the kid spoke up before him.

"He's car is busted. Can you go pick it up?"

He scratched his chin through his beard, "Hmm..sure i can go get it. What's the matter with it?"

The kid glanced her yes to Cry-Baby, obviously not knowing the answer.

"Um..it's been giving me trouble all week. I thought it might have gotten over heated but i cant get it to start."

"Hmm..alright ill give it a look-see." Phil patted the kid on the shoulder, "Go inside and get dinner started will ya sweetheart?"

The kid smiled and skipped to the house leaving the two men alone. Phil smiled at Cry-Baby who was obviously a little nervous. He walked over and pat his hand on Cry-Baby's back with a laugh. "Don't look so glum sonnie. We don't bite. Well most of us anyway." He let out another chuckle. "Where did you leave this car of yours?"

"Umm..It's still at school." Phil walked towards his garage and picked up a pair of gloves and his tool-box. "You go to the same school as Lilly-Anne?"

"Yeah." Cry-Baby was trying to find more words to say but was coming up short with Phil's Dad like demeanor. "I'm a senior."

"Thats good. Good. Good. Good." He stepped into his truck with his tools and cranked it. "Well you go on ahead inside. I'm sure if your hungry Lilly-Anne will fix you some dinner too. Don't mind Chrysta."

"Who's Chry-"

Before Crybaby could even ask, Phil had drove away and left Cry-Baby there staring after him. He glanced over to the old house, not sure he wanted to go inside at all, but a loud grumble of objection came from his gut reminding him of the last time he ate, which was yesterday.

Growling he stomped his way to the front of the house and saw the drunken devil was no where to be seen. He stared up at the screen door, the sent of something baking filling him with the willingness to move closer. He carefully stepped up the stairs trying not t make a sound and tip toed to the door. He stared at his boots and rapped his knuckles lightly against the wooden edges of the screen.

It flew open almost instantly to the kid looking at him brightly with a smile. "I was wondering when you would knock. Come in, come in. Dinner will be ready shortly."

He noticed she had removed he hair from her braids and now tied it up high in a kinky pony-tale. Her square school clothes had been swapped out for a white button down shirt with the sleeves rolled up and a pair of men's pajama bottoms, rolled up to her knees.

She shut the door behind him and he followed her through the dark wooden hallway to the glow coming from the door he presumed was the kitchen, from the smell that was coming from it. Once in the door she scurried over to the oven and stirred something in a large pot. "I hope you like chick and dumplings." She called. "Make yourself at home."

She pointed to a long table in the center of the room. It was old and scratched up, not that Cry-Baby cared about furniture conditions. His house with his aunt and uncle looked like a bar with bedrooms. He took a seat and looked at his surroundings silently. There was the kitchen. An old iron stove with various pots and pans hanging around it. By the door he entered was a sink and a few cabinets above it filled with what looked like bowls and cups. On the other side of the room was some large windows, cracked and tapped together, and moss and vines clinging the edges from the outside. Next to him he saw an open closet door filled with canned foods and assortments of food boxes. Finally did he spot the well hidden fridge behind another multi-colored tapestry.

Some foot steps sounded from up above them and started to descend. There must be some stairs somewhere, he thought. The steps grew louder and a girl emerged in the doorway.

Wait is that the drunken devil from before? She looked different now. Her mess of copper hair was damp and slicked out of her face. Her clothes were a clean white T-shirt and a pair of stripped blue mens boxers. The towel in her hand was rubbed against her wet hair trying to soak up some of the moisture.

So she still was dressed oddly, but she was certainly more recognizable as female. Cry-Baby even caught himself staring at her obviously female figure in that shirt and down her legs. Shaking his head he forced his eyes back to her face, which hadn't seemed to notice his presence yet.

"Something smells great. Whats for dinner little sister." She peeked a glance over the girls shoulder into the pot before the kid shoved her back. "Chicken and Dumplings..now go sit down and wait." The older one poked her lip out and shrugged and turned to sit down at the table, but her eyes grew wide and she froze when she spotted Cry-Baby staring.

"So you stayed after all huh? Well i owe you two bucks Lilly." She sat across from Cry-Baby with her sly smile plastered back on her face.

"What's that suppose to mean." He growled.

"Oh i bet Lilly here 2 dollars that you would have high tailed it back home by now."

"I told you he would stay. Nobody can say no to MY cookin." The girl smiled and winked at Cry-Baby, who averted his eyes ashamed. Why did his stomach have to get him into this kind of situation.

"Well hurry up I'm starving!"


End file.
